Journal of Analytical Toxicology,Vol. 16, January/February 19_

I }CaseReport , TissueDistributionofMethylenedi0xymethamphetamine

Timothy P. Rohrig and Richard W. Prouty Office of the ChiefMedicalExaminer,OklahomaCity,Oklahoma 'i

,; [ Abstract i jacentCaseto2.aTmotelwoadults,swimmingmale andpool.female,Severalweresyringesfound stuporouswith needlesad- Two casesof deathinvolving methylenedioxymethamphet- and severalsmall plastic bagscontaininga white powder were amine (MDMA)arereported; onecaseis afatal acuteoverdose also found next to the subjects.They were arousedby law eh. end the other is adrug-related death.The tissue distribution of forcementofficersandplacedunderarrest.Upon questioning, MDMAIsreported in both cases, male subject statedthat he andhis femalecompanionhadbeen "shooting Ecstasy" over a three-dayperiod. Two days subse.: quent to their arrest, the female subject committed suicide b_ hangingherselfwitha towelinjail. Introduction l Methylenedioxymethamphetamine (MDMA) is a ring-substi- tuted derivative of , which was first synthesized Materials and Methods · in the earl)' part of the century (1). MDMA was initially devel- i )_?,,/ oped as an anorectic, but the drug was never marketed as such be- Reagents. Methylenedioxymethamphetamine. methylene- _.. cause of its marked psychoactive properties. In the early 1970s, dioxyamphetamine, and methylenedioxypropylamphetamine ' L I a number of clinicians began prescribing MDMA as an adjunct to were purchased from Alltech-Applied Science. All other reagents psychotherapy (2). The drug induced a state of reduced anxiety were analytical reagent grade and were purchased from Fisher! % andlowereddefensiveness,allowingthetherapistto speedupto Scientificor Baxter. [ 7_ therapeutic process (3). In addition to its use in psychotherapy, Identificationprocedure. Blood and urine were screened f0__ ._ MDMA has become a popular recreational drug and is known to basic drugs with a modified Foerester and Mason procedure (9), the drug culture as Ecstasy, XTC, Adam, and MDM. MDMA pro- with alphaprodine and n-propylamphetamine as internal stan- duces psychoactive effects similar to those following a mild dose dards. The extract was initially analyzed on a Hewlett-Packard ,!_; of . The drug produces fewer of the visual, auditory, and (HP) 5890 gas chromatograph equipped with 15-m J&W DB-51 _ tactile hallucinations generally associated with other psychedelics, megabore column and a nitrogen-phosphorus detector (NPD). such as lysergic acid dJethylamide (4). In 1985, the United States The column operating conditions were 130--300°C at 10°C/rai_ .A._ Drug Enforcement Administration placed MDMA in Schedule I with a final hold of 5 min. The second chromatographic systena' ,_j_..; of the Controlled Substance Act (5), thus effectively removing its employed an HP 5890 equipped with a 15-m J&W DB-1 nar- use from clinical practice. Relatively few cases of death due to or rowbore column and a flame ionization detector (FID). Thc associated with MDMA use have been reported (6-8). This report column operating conditions were 100-300°C at 5°C/min. Ab describes the postmortem distribution of MDMA in an acute solute structural identification was obtained on an HP 5890 gas overdose death and a drug-related death, chromatograph coupled to a mass selective detector (HP Model ._ 5970 MSD), equipped with a 12-m HP-I capillary column. L//, '"-5 NormalAUTOTUNEprocedureswerefollowedforEl tuning. The column operating conditions were 80-300°C at 10°C/min. '0 Quantitation procedure. Quantitative analysis of methylene- Case Histories dioxymethamphetamine and methylenedioxyamphetamine was

c,,xx/ accomplished by gas chromatography (GC) using methylene-' ._ Case 1. A 35-year-old white male was reported to be "down the dioxypmpylamphetamine as the internal standard. The GC systen_ ¢ alley." Police amved and found the subject to be extremely in- (Case 1)was an HP 5890 equipped with aJ&W DB- 1narrowbore toxicated. The police returned to the scene approximately two column and an FID. The column was operated isothermally at

4 '74 hnextourstolaterthe andbody.foundTherehimwasdead.no traumaAn emptynoted,wine bottle was found a160J&W°C. TheDB-5GCmegaboresystem (Casecolumn2) andwasananNPD.HP 5890Theequippedcolumn owithper-

LI ¥ 1992 J_ of AnalyticalToxicology,Vol.16,January/Februar1992y

atingconditions were 150-190°C at 10°C/min. The peak height In Ca_e 1, the heart blood concentration of MDMA was 10.9 _ ratioof each analyte to internal standard was compared to a cai- mg/L This concentration is two orders of magnitude greater than ibrafion curve prepared from whole blood controls, peak concentrations seen in therapeutic dosing and is signifi- candy higher than the few overdose cases reported to date. In con- .A sideration of the circumstances surrounding the death, the autopsy , lC findings, and the toxicological studies, the cause of death was cer- tified as toxic effects of MDMA and ethyl alcohol, and the Results manner of death as accidental. Case 2 represents the tissue distribution of MDMA and MDA Case 1. The qualitative drug screen of the urine and blood in a traumatic death in a drug-abusing individual. The cause of was negative for acidic, basic, and neutral drugs, except for death was certified as hanging and the manner of death as suicide. methylenedioxymethamphetamine and methylenedioxyam- phetamine. The blood ethanol concentration was 0.21% w/v. No gross or microscopic anatomical cause of death was noted upon autopsy. Case2. The qualitative drug screen of the blood disclosed the Acknowledgments presence of methylenedioxymethamphetamine, methylene- dioxyamphetamine, benzoylecgonine, diazepam, and nordi- The authors are grateful to the Office of the Chief Medical Ex- azepam. No other acidic, basic, or neutral drugs were detected, aminer, Toxicology Laboratory staff for their analytical analyses, andthe blood was negative for ethyl alcohol. The autopsy find- and to Mrs. Barbara Mock for her assistance in the preparation of ·pus ad- ings were consistent with hanging, this manuscript. needles Results of the toxicological analysis for methylenedioxy- er were methamphetamine and methylenedioxyamphetanmine are pre- law eh. sented in Table I. Ling, the ad been References ; subse- cide by 1. ClandestinelyProducedDrugs, Analogues and Precusors,M. Discussion Klein, E SapJenza,H. McClain,Jr., and I. Khan, Eds., Department of Justice, Washington, D.C., 1989 pp. 195-206. A review of the literature revealed little information regarding 2. , Marijuana, Designer Drugs: Chemistry, Pharma- _he distribution of MDMA in man (6-8). The reported blood Ecodlogys., CRC,and BocaBehaviorRato,nK,.KFl.oRrieddda, a,198C.9A,.pWalker,p. 181-8a4nd. G. Barnett, concentrations in acute fatal overdoses have ranged from 1.0-2.0 3. D.E. Nichols. Differences between the mechanism of action of mg/L. In an experimental trial following a single oral dose of 50 MDMA, MBDB and the classic hallucinogens. Identification of a rog,a peak plasma concentration of MDMA was O.106 mg/L has new therapeutic class: Entactogens. J. Psychoactive Drugs thylene- been reported (6). 18(4): 305-13 (1986). etamine 4. R.V. Suarez and R. Riemersma. "Ecstasy" and sudden cardiac reagents Table I. Tissue Distribution (mg/L) death. Am. J. Forens. Med. and Path. 9(4): 339-41 (1988). n Fisher 5. J.C. Lawn. Fed. Reg. 50: (105): pp 23118-20, May 31, 1985. Specimen MDMA* MDA* 6. K. Verebey, J. Alrazi, and J.H. Jaffe. The complications of ·ened for "ecstasy" (MDMA). J. Am. Med. Assoc.259:1649-50 (1988). dure (9 Case1'* Heartblood 10.9 <0.5 7. G.P. Dowling, E.T. McDonough, and Re. Best. "Eve" and hal stan- Fem0rablot od 2.8 ND: "Ecstasy": A report of five deaths associated with the use of Liver 20.2 ND MDEA and MDMA. d. Am. Med. Assoc. 257(12): 1615-17 -Packard Brain 13.7 ND (1987). .W DB-5 8. R. Best. Deaths associated with MDMA and MDME in Dallas r (NPD). Case2t Femorabll ood 0.58 0.10 lOde/rain Liver 1.8 <0.33 county. Presented at the spring meeting of the Southwestern Brain <1.6 ND Association of Toxicologists,Austin, Texas,April 1990. ic system 9, E.H. Foerester and MF. Mason. Preliminarystudies on the use )B- l oar- ·'. NoMOOM&tllemetClrugsr hylenecletecdtoxymeted thamoMOhetammeAme: t_y;lened_oxyampnetamme of n-butylchloride as an extractantin a drug screening procedure. ID). The t Bide0 (heart): clrazepam. 034 .g/rnL; norchaze0am. 0.66 .g/mL: benzoytecgonme J. Forens. Sci. 19(1): 155-62 (1974). <0 20 _OjmL 'min. Ab- : NDn:oclet tectecl 5890 gas -- Manuscript received September 30, 1990. {P Model column. EI tuning. )°C/min. lethylene- mine was mthylene- SC system arrowbore ermally al ipped with umn oper-

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